Vacation rentals in Longboat Key

Apartment in Longboat Key

4.95 out of 5 average rating, 110 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

4.88 out of 5 average rating, 105 reviews

Beautiful Panoramic Gulf and Sunset Views.

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

4.91 out of 5 average rating, 123 reviews

Home in Longboat Key

Longboat Key Beach House

This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. A 3 minute walk to the beach and to the bay, this house is within a block of restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has 10 HarTru Tennis Courts, a junior Olympic POOL, gym, bicycle rental and tiki bar. Only Minutes to Holmes, Bradenton and Coquina Beaches.

Superhost

4.79 out of 5 average rating, 114 reviews

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

4.91 out of 5 average rating, 185 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

4.99 out of 5 average rating, 154 reviews

Silver Sands: Open Monday & Tuesday $225/nt +Fees!

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Superhost

Apartment in Longboat Key

5 out of 5 average rating, 4 reviews

Waterfront 2BR 2BA | Pool - 10 min walk to Beach

A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.

Guesthouse in Bradenton Beach

4.99 out of 5 average rating, 186 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

4.88 out of 5 average rating, 113 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Superhost

4.79 out of 5 average rating, 240 reviews

SRQ/Longboat Key Beach - kid friendly/romantic B1

Beachfront on beautiful Longboat Key, this condominium, unit 234, offers all the amenities of a large hotel with the privacy and seclusion that has Silver Sands guests returning each year. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy a complimentary chaise lounge and beach umbrella while breathing in the fresh salt-water air.

4.98 out of 5 average rating, 278 reviews

Guesthouse in Sarasota

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.